Dare Me (Henry Bowers x Reader)

Grow up already

1994 Derry

I laugh watching Richie and the kids I've watch from up walk across the stage of graduation. As their hats fly high and cheers erupt through the football field I see Richie and Eddie jumping and hugging happily.

"You did it!" I run over to my brother in the parking lot hugging onto him. "Ah, (y/n) get the fuck off I need to be cool for the older ladies now!" "Beep beep Richie!" Our parents come over and congratulate him as well. 

Richie and I soon end up at the local diner treating ourselves to cakes and cookies. "What do you plan to do Richie?" He sighs and looks at me with worry. "Rich?" "I have to tell you something." "Oh my god, you didn't get someone pregnant did you?" "(y/n), no! I'm leaving to go to New York. I'm going to pursue a career in stand up. I have a few shows in the next months at some of the bars until I get started." My blood runs cold. "You're leaving Derry?" He nods with a smile. "You should come with me." "Richie, you know I can't. I have to watch out for mom. You know how her mind is, and Dad doesn't care to even pay attention to the bills. Plus I need to see-" "Henry. Now I get it, (y/n)." Richie snaps.

"What the hell? Why are you saying it like that?" "Because (y/n), you've been worried about him since he was locked up 5 years ago! He's not getting out and he's not getting better. I know you two had some weird thing going on when we were younger, but damn-it (y/n). I want you happy." I narrow my eyes at him. "You do know the only reason most of us are alive is because of him. He was there too, Richie!" "He also murdered his own father." "He didn't mean to. Penny-" "DON'T!" Richie hisses. He grabs his coat and throws money on the table for our meal. "Grow up (y/n). We were kids. Just scared little kids who played in the wrong fucking game. It's over. You need to move on." He swings the door open and walks out.

I huff and gather my things as well going to the one place I know will make me calm. Ironically it is the hospital. I walk in seeing the nurses shoot me sad smiles. "Evening ladies." I scan my pass and walk through the doors.

I sit next to Henry as he watches TV. He turns his head smiling. "You're here." I loop my arm around his and smile back. "Sorry, I'm a little late. Richie's graduation was today."

"Trashmouth graduated?" I nodded smiling. "So... it's been a while." "It's been 5 years Henry." he looks away nodding. "I knew that."

Did he?

"Where is your necklace?" "Don't worry." I laugh pulling it from under my shirt. "I never take it off." Henry kisses my forehead lightly. "I love you." "I love you too, Henry." He laughs shaking his head. "You shouldn't." I scoff looking into his beautiful eyes. "Why not?"

"You have a life outside of here. Where are you even working now?" I shrug, "I still waitress, and I work in the library." "That pays bills?" I look away knowing the answer. "You can't stay here, (y/n). Spending 10 minutes a day with me is just... fucking stupid. I'm sorry. I don't want that for you." Tears fill my eyes "You don't know what you're talking about Henry. I'm just-" "Just the most beautiful woman I've ever seen who deserves more than this. You're 21 (Y/n). Where do you go from here?" "I grow old here. I take care of you and make sure you're okay. We have each other." Henry smiles at me shaking his head sadly. "I won't tell you what to do, but I will say you're stupid, Tozier." "I'm not the one who still has a mullet." I laugh blinking my tears away. Henry grabs my hand looking me in the eyes. "I love you, but you've got more planned." I look at the clock and see my time is up. "I'll be back tomorrow, Henry." He smiles kissing my hand. "See you later, Tozier."

1999 Derry

"Henry look!" I slide him the picture of me that was published in the newspaper a couple of weeks prior.

"Voted Derry's Local Sweetheart. (Y/n) Tozier, local since birth has been spreading joy around the town anyway she can. From visiting the local patients at the hospital, baking cakes for the elderly, or helping town officials clean after events! We are thankful for our Sweetheart!"

Henry smiles reading it. "Look they put a picture of us too." He points to a picture from a couple of years prior. "You look handsome. Happy even." "Well look who I'm with. Of course I'm happy."

I kiss his cheek and lean into him while the workers don't pay any mind. "Richie called last night." "Yeah?" I nod smiling "He's doing good. Says he has been doing well. He gets a lot of laughs from the crowd. He says he is going to a signing meeting next week so he could actually get picked up by someone big." "Who knew Trashmouth would go so far." "Yeah. I'm proud of him."

"No one can take the place of the Derry Sweetheart. Way cooler than someone telling jokes all day." "Plus he doesn't even write his own stuff! He stole it from me when we were younger!" We laugh and continue the short time we have together.

---

I lay on the couch while my mother knits yet another sweater for Richie. "You know he has 6 sweaters he already doesn't wear? I think you can cut back a bit, mom." "Honey, your brother lives in New York! It is chilly there!" "And the dumbass still will wear shorts in the snow!" "Beep beep, (y/n)."

My phone rings and I answer immediately seeing the contact. "Sup lil bitch!" "Sup bro!" My brother and I laugh through the line. "I have some news for you sis, and if you don't take it I will be super pissed and never talk to you again." "Wow, then I should listen up." "Yes! So listen. Mom sent me the picture of you, and while I was doing a show I passed it around and you'll never guess what happened!" "Then I guess you should tell me!" "JUNO WANTS YOU TO COME HERE AND MODEL FOR FAIRWAY MAGAZINE!" I look at my mom and hang my mouth open.

"Is that your brother? I need to talk with-" "JUNO? THE JUNO!" "YES! THE JUNO! You need to come here for a test shoot Monday if you want to do this!"  "Monday? Richie today is Thursday! I can't just-" "Yes, yes you fucking can and you are. I am getting you out of Derry. I'm booking you a ticket you can thank me later. Tell mom to stop sending me sweaters! I still wear shorts out here!" "I ALREADY TOLD HER THAT!"

---

"Henry, I have to tell you something." "Oh yeah? What is it?" "Richie called me and he wants me to come visit him for a little bit." "Are you doing something there?" I smile and nod. "Juno from Fairway Magazine wants to meet with me and have a photoshoot! They might want me to model full time!" Henry's eyes grow wide and he smiles at me. "A fucking model?" "Well...yeah... Why?"

Henry smirked and leaned in. "Can't believe I've been fucking a model." I push his shoulder away and laugh. "Shut up Bowers!"

"You should go. In a way, I'll finally get to show off my girl." Henry stands up clapping his hands. "Alright! My girl here is going to be a model!" His fellow inmates cheer and laugh. "Henry, stop." I laugh pulling him down as he smiles. "You're going to be an amazing model, baby." I blush to grad his hands. "You know I won't be able to see you as much, right?" Henry's eyes fell, but he kissed me happily. "When it's for you, I don't care. I just ask you don't forget about me." I kiss him once more quickly. "Never."